US2346808A - Lubricant - Google Patents

Lubricant Download PDF

Info

Publication number
US2346808A
US2346808A US333772A US33377240A US2346808A US 2346808 A US2346808 A US 2346808A US 333772 A US333772 A US 333772A US 33377240 A US33377240 A US 33377240A US 2346808 A US2346808 A US 2346808A
Authority
US
United States
Prior art keywords
oil
phenol
metal
alcohol
alkyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
Application number
US333772A
Other languages
English (en)
Inventor
Winning Carl
John G Mcnab
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Standard Oil Development Co
Original Assignee
Standard Oil Development Co
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to NL83422D priority Critical patent/NL83422C/xx
Priority to NL64743D priority patent/NL64743C/xx
Application filed by Standard Oil Development Co filed Critical Standard Oil Development Co
Priority to US333772A priority patent/US2346808A/en
Application granted granted Critical
Publication of US2346808A publication Critical patent/US2346808A/en
Priority to FR917395D priority patent/FR917395A/fr
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
    • C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2203/00—Organic non-macromolecular hydrocarbon compounds and hydrocarbon fractions as ingredients in lubricant compositions
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/16—Paraffin waxes; Petrolatum, e.g. slack wax
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2205/00—Organic macromolecular hydrocarbon compounds or fractions, whether or not modified by oxidation as ingredients in lubricant compositions
    • C10M2205/18—Natural waxes, e.g. ceresin, ozocerite, bees wax, carnauba; Degras
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/021—Hydroxy compounds having hydroxy groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/025—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/02—Hydroxy compounds
    • C10M2207/023—Hydroxy compounds having hydroxy groups bound to carbon atoms of six-membered aromatic rings
    • C10M2207/027—Neutral salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/04—Ethers; Acetals; Ortho-esters; Ortho-carbonates
    • C10M2207/046—Hydroxy ethers
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/08—Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/09—Metal enolates, i.e. keto-enol metal complexes
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/281—Esters of (cyclo)aliphatic monocarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/282—Esters of (cyclo)aliphatic oolycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/283—Esters of polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/28—Esters
    • C10M2207/286—Esters of polymerised unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2207/00—Organic non-macromolecular hydrocarbon compounds containing hydrogen, carbon and oxygen as ingredients in lubricant compositions
    • C10M2207/40—Fatty vegetable or animal oils
    • C10M2207/404—Fatty vegetable or animal oils obtained from genetically modified species
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/04—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions containing carbon, hydrogen, halogen, and oxygen
    • C10M2211/042—Alcohols; Ethers; Aldehydes; Ketones
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2211/00—Organic non-macromolecular compounds containing halogen as ingredients in lubricant compositions
    • C10M2211/06—Perfluorinated compounds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
    • C10M2215/06—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings
    • C10M2215/062—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to carbon atoms of six-membered aromatic rings containing hydroxy groups bound to the aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/20—Containing nitrogen-to-oxygen bonds
    • C10M2215/202—Containing nitrogen-to-oxygen bonds containing nitro groups
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions
    • C10M2215/24—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant Compositions having hydrocarbon substituents containing thirty or more carbon atoms, e.g. nitrogen derivatives of substituted succinic acid
    • C10M2215/26—Amines
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/084—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/086—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing sulfur atoms bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/08—Thiols; Sulfides; Polysulfides; Mercaptals
    • C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
    • C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
    • C10M2219/089—Overbased salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/102—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon only in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/106—Thiadiazoles
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2219/00—Organic non-macromolecular compounds containing sulfur, selenium or tellurium as ingredients in lubricant compositions
    • C10M2219/10—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring
    • C10M2219/104—Heterocyclic compounds containing sulfur, selenium or tellurium compounds in the ring containing sulfur and carbon with nitrogen or oxygen in the ring
    • C10M2219/108—Phenothiazine
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/041—Triaryl phosphates
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/02—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having no phosphorus-to-carbon bonds
    • C10M2223/04—Phosphate esters
    • C10M2223/042—Metal salts thereof
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
    • C10M2223/00—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions
    • C10M2223/06—Organic non-macromolecular compounds containing phosphorus as ingredients in lubricant compositions having phosphorus-to-carbon bonds
    • C10M2223/061—Metal salts
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/04—Groups 2 or 12
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/06—Groups 3 or 13
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/08—Groups 4 or 14
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/14—Group 7
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2010/00—Metal present as such or in compounds
    • C10N2010/16—Groups 8, 9, or 10
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2030/00—Specified physical or chemical properties which is improved by the additive characterising the lubricating composition, e.g. multifunctional additives
    • C10N2030/12—Inhibition of corrosion, e.g. anti-rust agents or anti-corrosives
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2060/00—Chemical after-treatment of the constituents of the lubricating composition
    • C10N2060/04—Oxidation, e.g. ozonisation
    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
    • C10N2070/00—Specific manufacturing methods for lubricant compositions
    • C10N2070/02—Concentrating of additives

Definitions

  • M-YAr (X) a where M is a metal, Y is an element in the right hand side of group 6 of the periodic table (Mendeleefi), Ar is an arctic nucleus which contains like or unlike substituents X, n in n .11 her, replacing nuclear hydrogen, n being at least one.
  • the substituents X may be organic, inorganic, or both.
  • they may be 1 radicals or groups containing one or more of the non-metallic elements belonging to oups V, Vi, and VII of the periodic system (Mendeleefi): nitrogen, phosphorus, oxygen, sulfur, a halogens, as in amino, nitro, phosphite, phosphate, hydroxy, aikoxy, sulfide, thioether. mercapto, chloro groups, and the like, or they may be organic radicals containing one or more of the inorganic groups.
  • the metal compounds to be used in this invention may be said to be etal salts oi phenols and thio-phenols and derivatives thereof.
  • non-phenolic groups a tached to the metal are indicated broadly by R in the following types of compositional formulas, which broadly represent barium derivatives of substituted phenolic compounds containing the characteristic compositional grouping described:
  • Group A Some of these compounds when employed in high temperature lubrication service tend to corrode such sensitive engine parts as copper-lead and cadmium-silver bearings. This characteristic can usually be corrected by including, in the lubricating composition, suitable anti-oxidants or other anti-corrosion agents, e. g. benzyl paraamino phenol, alpha naphthol, tertiary amyl phenol sulfide, triphenyl phosphite, dibutyl amine, etc. It may be mentioned that metal soaps of carboxylic acids are considerably more corrosive than the phenolic salts of this invention and that their corrosiveness is less amenable to correction by the use of anti-oxidants, etc.
  • suitable anti-oxidants or other anti-corrosion agents e. g. benzyl paraamino phenol, alpha naphthol, tertiary amyl phenol sulfide, triphenyl phosphite,
  • Group B These preferred phenolates may also contain sulfur in other positions or groups at the same time as in the places shown in the formulas in Group B. Furthermore, the formulas in Group A may have sulfur incorporated therein in other ways than as shown in Group B, for instance, in the hydrocarbon groups. More broadly it may be stated that inorganic substituents, particularly J negative inorganic groups containing non-metallic elements of groups V, Vii, and VII of the Mendeleeif Periodic System, beneficially influence the phenolates by increasing their potency for stabilizing the lubricating oils and by making the phenolates, in themselves, more stable, as for instance, against hydrolysis,
  • R represents an organic group which may be either aryl, alkyl, alkaryl, aralkyl or cycloalkyl, and which may contain substituent groups such as halogen, particularly chlorinejnitro, nitroso, amino, hydroxy, carboxy, alkoxy, aroxy, mercapto. and the like, but" R preferably is or contains an alkyl or alkenyl group and preferably contains at least 4 carbon atoms but may contain many more, such as 8, 10, 16,18, etc.
  • the configurations f the compounds are not limited to certain positions for the substituent groups, for these may be in ortho, para, or meta relations to one another. Also, the substituents, x, in broader formulas discussed previously, in any aromatic nucleus may be alike or different.
  • the aromatic nucleus may be polycyclic as in naphthalene, phenanthrene, diphenyl, etc. Where oxygen occurs, it may be replaced by sulfur, selenium, or tellurium, as in the case of thio-phenolic compounds.
  • Alkyl phenolates e. g. salts of diisobutyl phenol, salts of octadecyl phenol, salts of ditert. amyl phenol.
  • Alkyl chlorophenolates e. g. salts of 2-chloro-4-octadecyl phenol, salts of 2, 6-dich1oro-4-diisobutyl phenol, salts of 6- chloro-2, 4-ditert. amyl phenol.
  • the compounds of this invention preferably have the general empirical formula:
  • M is the metal, 11. is one half the valence of the metal, a: is 1 or more, R represents one or more alkyl groups, having enough carbon atoms, preferably a total in the molecule.of at least 10, to insure solubility of the compounds in mineral oil.
  • the metal phenolates have been preferably prepared from phenolic compounds readily obtainable by alkylation of the simple phenols and cresols or by extraction from high-boiling petroleum oils.
  • Suitable synthetic alkyl phenols for preparing the desired phenolate are those containin one or more substituents which provide a desired number of carbon atoms in groups having the form of straight chains, branched chains, or rings.
  • Mono-alkyl or poly-alkyl phenols are synthesized conveniently by alkylating a phenol with branched chain olefin polymers, such as diisobutylene, triisobutylene, di-tert-amylene, or other suitable agents, such as alcohols, alkyl sulfates, alkyl phosphates, or alkyl halides, thereby forming carbon-to-carbon bonds between the aromatic nucleus and the alkyl group.
  • the alkylation reaction involves a condensation of olefins with the simple phenols, the reaction being catalyzed by anhydrous metal halides, sulfuric acid, phosphoric acid, or certain activated clays.
  • olefinic reactants refinery gases containing propylene, butylenes, amylenes, etc., are economicall useful, although individual olefins, e. g., isobutylene, iso-amylene, diisobutylene, triisobutylene, etc., or olefin-containing mixtures from other sources may be used.
  • the reaction temperature is usually controlled to avoid side reactions.
  • sulfuric acid a liquid phase reaction at relatively low temperature is preferred; with phosphoric acid the reaction may be carried out in the vapor phase.
  • Petroleum phenols are considered to contain polymethylene or cycloalkyl substituents, as evidenced by their hydrogen and carbon analysis.
  • the petroleum phenols are obtained by extraction of various stocks, chiefly cracking process heating oil stocks, with caustic soda, and acidification of the alkaline extract with a weak mineral acid followed by a non-destructive distillation if desired.
  • alkylated phenols may be procured for preparing the phenolates: tort-amyl phenol,
  • diisobutyl phenol is meant phenol having a branched octyl group, which may be obtained by reacting phenol with diisobutylene; this product might also be called tetramethylbutyl phenol.
  • Inorganic substituents are introduced into alkyl phenols by well-known methods; For example, an alkyl phenol, e. g. tert-amyl phenol, is reacted with sulfur monochloride, sack, in about a 2:1 mole ratio and preferably in a solvent such as dichlorethane, to produce the alkyl phenol disulfide.
  • an alkyl phenol e. g. tert-amyl phenol
  • SClz sulfur dichloride
  • the alkyl phenols are given a thioether linkage; about 0.5-2 moles, preferably 1.25 to 1.5 moles of SClz are used per two moles of alkyl phenol.
  • reaction with the, sulfur chlorides is usually attended by the introduction of some chlorine to the molecule so that in a mixture of reaction products a varying proportion of the molecules contain chlorine as well as sulfur. Because the chlorine may be present in very minor proportions, the reaction products are referred to in this invention as phenol sulfides, for convenience, but it is to be understood that they may contain chlorine as well.
  • Alkyl chlorphenols are also obtained by chlorination, preferably controlled to replace nuclear hydrogen by a chloro group. This may be accomplished by chlorinating the phenol before alkylation. In such a manner, for example, 2-chloro-4-tert amyl phenol can be produced. Nitro substituents are introduced readily into the aromatic nucleus by direct nitration, and nitro substituents can be reduced to amino groups. It is to be understood, however, that the preparation of substituted phenolic compounds which have been described does not form part of this invention and that any of the well-known methods-for their production may be used.
  • the various products obtained may be purified, if desired, by fractional crystallization, extrac-. tion, selective precipitation, etc. Also, impurities may be removed by treatment with suitable adsorptive agents such as clay.
  • the amount of metal compound to be used should be between the approximate limits of 0.02 to 2.0%, and preferably from 0.1 to 1.0%, the exact amount to be used depending to a certain extent upon the particular compound, the amount of higher alcohol used. the character of the mineral oil base and the operating conditions of the engine in which the lubricant is to be used.
  • a lubricating 011 base stock prepared from naphthenic or aromatic crudes to have-a Baybolt viscosity at 210' I". of 45 to seconds and a viscosity index of 0-50.
  • the additives are to be employed in gasoline engine (spark ignition) service, they will probably find most widespread application to motor oils of '75 viscosity index and over.
  • Products prepared synthetically by chemical processes may also .be used such as alcohols prepared by the oxidation of petroleum hydrocarbons, e. g. paraffin wax; petrolatum, etc.
  • Table 1 also shows that a barium diisobutyl phenolate. (test 11) had an effect substantially similar to that of the metal alkyl phenol sulfide in reducing the pour point of a mineral oil blend containing some stearyl alcohol.
  • compositions of this invention can also be used for a number of other purposes, for example as flushing compositions for cleaning a crankcase of an internal combustion engine (for which purpose an oil base stock should be used which has a lower viscosity than that of the lubricating oils discussed hereinabove. e. 8. gas oil, mineral seal oil or even kerosene).
  • the inspection record of these three samples is EXAMPLE 3 blended with 1.0% magnesium tertiary amyl phen01 sulfide and a second blend 0! the same comfi fiflgi fffif fg gfi flm 25 53: pound with 0.5% stearyl alcohol were tested for 60 and a second blend of the same compound to hours. Both compounded oils proved outstanding which 0.5% oi a stem] al hol wa added were in maintaining engine parts in a clean condition tested for 60 hours in a Caterpillar Diesel engine.
  • Na hthenic base oil 1.07 m esium ter tiar amyl phenol inning? 60 1.14 5 :s 8.00 9.50 0.38 1.50 Ditto+0.5% stearyl alcohol 60 0.87 4.5 9.00 4.75 0.06 0.75
  • EXAMPLE 7 Another series of caterpillar Diesel engine 25 Some tests were made on a Hercules DRXB tests was made to compare the eilect on the engine performance of the use of blends of barium gisz ig g fi g 1:35: 528 3;: diisobutyl phenol sulfide alone as well as with e a small amount of a higher alcohol. The results results of 84-hour tests with a reference oil and of these tests are shown in Table m.
  • test 3 a blend containing stearyl 7 g fi gggg f gufi g gfggf base Stock having a c i y o alcohol (test 3). The results show that the use 11111111111 salt of dilsobutyl phenol sulfide.
  • EXAMPLE 9 An important property possessed by certain compounded lubricating oils is their ability to hold in suspension or disperse carbonaceous or sludge-like deposits formed in the oil during the operation of an internal combustion engine. By preventing the coagulation and deposition of such materials on the surfaces of the engine parts these eflicient compounded oils maintain the engine in a clean condition, free from deposits and stuck rings.
  • this sludge-dispersing quality of lubricating oils the following laboratory test has been employed: A 450 gram sample of the oil to be tested is heated to 225 F. and agitated in a mixer. 30 grams of carbon black are added gradually to the oil during agitation and the mixture agitated thoroughly for an additional half-hour period.
  • the suspension is then transferred to a graduated 500 cc. cylinder, and allowed to stand for 22 hours in a constant temperature bath at 200 F., and for an additional two-hour period at room temperature.
  • the carbon black settles from the oil leaving a clear supernatant layer, the volume of which is measured in cubic centimeters.
  • the carbon black remains suspended throughout the entire volume of oil in the cylinder.
  • the effectiveness of a sludge dispersing agent is evaluated by determining the concentration oi carbon black remaining in suspension in a given volume of oil near the top of the cylinder. For this purpose a 10 cc. sample of the suspension is pipetted from a point 25 cc. below the surface of the liquid in the cylinder; diluted to an appropriate volume (usually 250 cc.) with naphtha; and the concentration of carbon black is determined as milligrams per cubic centimeter by colorimetric comparison with a standard suspension.
  • the data recorded below illustrate the influence of stearyl alcohol in improving the sludge dispersing properties of metal containing addition agents in lubricating oils:
  • cetyl alcohol 1 Salt of tertiary amyl phenol sulfide 'Commercially available mixture of primary, secondary and tertiary aliphatic alcohols having 17 carbon atoms.
  • a lubricant comprising a major proportion of mineral oil base stock, 0.01% to 5% of an aliphatic alcohol having at least 8 carbon atoms, and 0.02% to 2% of an oil-soluble metal salt of an alkylated phenol.
  • a lubricant comprising a major proportion of mineral oil base stock, about 0.01 to 5.0% of an alcohol having at least 8 carbon atoms, and a small amount of an oil-soluble metal salt of an alkylated phenol sulfide.
  • a lubricant comprising a major proportion of mineral oil base stock, about 0.01% to 5% 0! an alcohol having at least eight carbon atoms and between 0.02% to 2% of an oil soluble metal salt of an alkylated phenol sulfide which has easentially the general formula:
  • M is a metal
  • R represents at least 1 alkylgrcup attached to Ar
  • Ar is an aromatic nucleus
  • 1: is 1-2
  • n is one half the valence of the metal.
  • Lubricant according to claim 3 in which there are a total of at least 10 carbon atoms in the alkyl portion of the metal compound.
  • Lubricant according to claim 3 in which M" is a metal selected from the group consisting of an alkali metal, alkaline earth metal, aluminum, zinc, tin, cadmium, cobalt and nickel.
  • Ar is a benzene nucleus
  • R is an alkyl group having at least 5 carbon atoms
  • z is 1-2.
  • Lubricant according to claim 3 in which the metal compound used is barium di-isobutyl phenolate sulfide.
  • a lubricant comprising a major proportion of a mineral oil base stock. 0.01% to 5% of an alcohol having at least 8 carbon atoms, and 0.02% to 2% of an alkaline earth metal alkyl phenol sulfide.
  • Lubricant according to claim 8 in which the metal compound is magnesium tertiary amyl phenol sulfide.
  • Lubricant according to claim 8 in which the metal compound is barium di-isobutyl phenol sulfide.
  • a lubricant comprising a major proportlon or a mineral oil base stock, 0.01% to 5% of an aliphatic alcohol having 72 to 20 carbon atoms, and 0.02% to 2% of a divalent metal salt of a phenol sulfide having the general formula:
  • Ar is a benzene nucleus
  • R is an alkyl group having at least 5 carbon atoms
  • a lubricant comprising a major proportion of mineral 011 base stock, 0.01% to "5% of higher alcohol, and 0.02% to 2% of an oil-soluble metal .salt or a reaction product of a sulfur halide with oil-soluble metal salts of alkylated phenols and oil-soluble metal salts of alkylated phenol sulfides.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Lubricants (AREA)
US333772A 1940-05-07 1940-05-07 Lubricant Expired - Lifetime US2346808A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
NL83422D NL83422C (en(2012)) 1940-05-07
NL64743D NL64743C (en(2012)) 1940-05-07
US333772A US2346808A (en) 1940-05-07 1940-05-07 Lubricant
FR917395D FR917395A (fr) 1940-05-07 1945-11-14 Lubrifiant

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US333772A US2346808A (en) 1940-05-07 1940-05-07 Lubricant

Publications (1)

Publication Number Publication Date
US2346808A true US2346808A (en) 1944-04-18

Family

ID=23304198

Family Applications (1)

Application Number Title Priority Date Filing Date
US333772A Expired - Lifetime US2346808A (en) 1940-05-07 1940-05-07 Lubricant

Country Status (3)

Country Link
US (1) US2346808A (en(2012))
FR (1) FR917395A (en(2012))
NL (2) NL64743C (en(2012))

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2419360A (en) * 1944-12-21 1947-04-22 Standard Oil Dev Co Lubricating oil composition
US2420893A (en) * 1944-01-04 1947-05-20 Standard Oil Dev Co Compounded lubricating oil
US2447607A (en) * 1944-12-30 1948-08-24 Standard Oil Dev Co Lubricant
US2459063A (en) * 1946-05-09 1949-01-11 American Cyanamid Co Divalent metal salts of halogen substituted phenylol sulfides
US2514186A (en) * 1945-10-22 1950-07-04 Firestone Tire & Rubber Co Antimony phenol sulfides
US3038877A (en) * 1960-02-18 1962-06-12 Eastman Kodak Co Dialkyl tin bis-(poly-halogenated phenates) and halogenated synthetic resins containing same
US3200135A (en) * 1959-07-29 1965-08-10 Sterling Drug Inc Copper, cadmium, and zinc salts of halo-2, 2'-dihydroxydiphenyl sulfides and sulfoxides
US4066561A (en) * 1974-01-04 1978-01-03 Mobil Oil Corporation Organometallic compounds and compositions thereof with lubricants
US4083792A (en) * 1976-01-02 1978-04-11 Mobil Oil Corporation Overbased metal complexes and compositions thereof with lubricants
US4151100A (en) * 1977-11-21 1979-04-24 Mobil Oil Corporation Novel cobalt thiobis(alkylphenolates) and antioxidant compositions thereof

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2420893A (en) * 1944-01-04 1947-05-20 Standard Oil Dev Co Compounded lubricating oil
US2419360A (en) * 1944-12-21 1947-04-22 Standard Oil Dev Co Lubricating oil composition
US2447607A (en) * 1944-12-30 1948-08-24 Standard Oil Dev Co Lubricant
US2514186A (en) * 1945-10-22 1950-07-04 Firestone Tire & Rubber Co Antimony phenol sulfides
US2459063A (en) * 1946-05-09 1949-01-11 American Cyanamid Co Divalent metal salts of halogen substituted phenylol sulfides
US3200135A (en) * 1959-07-29 1965-08-10 Sterling Drug Inc Copper, cadmium, and zinc salts of halo-2, 2'-dihydroxydiphenyl sulfides and sulfoxides
US3038877A (en) * 1960-02-18 1962-06-12 Eastman Kodak Co Dialkyl tin bis-(poly-halogenated phenates) and halogenated synthetic resins containing same
US4066561A (en) * 1974-01-04 1978-01-03 Mobil Oil Corporation Organometallic compounds and compositions thereof with lubricants
US4083792A (en) * 1976-01-02 1978-04-11 Mobil Oil Corporation Overbased metal complexes and compositions thereof with lubricants
US4151100A (en) * 1977-11-21 1979-04-24 Mobil Oil Corporation Novel cobalt thiobis(alkylphenolates) and antioxidant compositions thereof

Also Published As

Publication number Publication date
NL64743C (en(2012))
NL83422C (en(2012))
FR917395A (fr) 1947-01-06

Similar Documents

Publication Publication Date Title
USRE22910E (en) E-oxcxs-m
US2409687A (en) Sulfur and metal containing compound
US2418894A (en) Compounded lubricating oil
US2591577A (en) Lubricating oil containing disulfide derivatives of organo-substituted thiophosphoric acids
US2552570A (en) Oxidation resisting hydrocarbon products
US2451345A (en) Compounded lubricating oil
US2402448A (en) Chemical process
US2362293A (en) Lubricant
US2406564A (en) Compounded lubricating oil
US2346808A (en) Lubricant
US2451346A (en) Compounded lubricating oil
US2658062A (en) Mineral oil additive
US2743235A (en) Mineral oil composition
US2354536A (en) Lubricating oil composition
US2530339A (en) Compounded petroleum hydrocarbon products
US2362292A (en) Lubricant
US2293445A (en) Lubricant with high temperature stability
US2483505A (en) Compounded lubricating oil
US2409726A (en) Lubricant composition
US2362291A (en) Lubricant
US2689258A (en) Reaction of terpenes with thiophosphorous acid esters and products thereof
US2420893A (en) Compounded lubricating oil
US2480664A (en) Lubricating oil composition
US2852540A (en) Oil soluble alkali and alkaline earth metal salts of p-acylamino phenols
US2734867A (en) Additive for lubricants